Trifluoroacetic acid → (6-{4-[6-(4-Fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-3-(R)-methyl-piperazin-1-yl}-5-methyl-pyridin-3-yl)-acetic acid

HRID 2195063Notes

Reaction equation

HRID 2195063 reaction equation
C([O:5][C:6](=[O:41])[CH2:7][C:8]1[CH:9]=[N:10][C:11]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[C:25]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[N:24]=[C:23]([N:34]4[CH2:38][CH2:37][CH2:36][C@H:35]4[CH3:39])[N:22]=3)[C@H:17]([CH3:40])[CH2:16]2)=[C:12]([CH3:14])[CH:13]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:33][C:30]1[CH:29]=[CH:28][C:27]([C:25]2[N:24]=[C:23]([N:34]3[CH2:38][CH2:37][CH2:36][C@H:35]3[CH3:39])[N:22]=[C:21]([N:18]3[CH2:19][CH2:20][N:15]([C:11]4[N:10]=[CH:9][C:8]([CH2:7][C:6]([OH:41])=[O:5])=[CH:13][C:12]=4[CH3:14])[CH2:16][C@H:17]3[CH3:40])[CH:26]=2)=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59168306(6-{4-[6-(4-Fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-3-(R)-methyl-piperazin-1-yl)-5-methyl-pyridin-3-yl)-acetic acid tert-butyl ester

Product 1

HCID 59168364(6-{4-[6-(4-Fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-3-(R)-methyl-piperazin-1-yl}-5-methyl-pyridin-3-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir a solution of (6-{4-[6-(4-fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-3-(R)-methyl-piperazin-1-yl}-5-methyl-pyridin-3-yl)-acetic acid tert-butyl ester (210 mg, 0.375 mmol) and 1 mL of TFA in DCM (10 mL) at room temperature for 16 h. Concentrate and partition between EtOAc and sat. NaHCO3. Dry the organic layer (Na2SO4) and concentrate under reduced pressure. Purify using flash chromatography eluting with MeOH-DCM (1:19) to give the title compound.

Workup

  1. concentrationConcentrate
  2. custompartition between EtOAc and sat. NaHCO3
  3. dry with materialDry the organic layer (Na2SO4)
  4. concentrationconcentrate under reduced pressure
  5. customPurify
  6. washeluting with MeOH-DCM (1:19)

Sources & evidence

ORD record
ord-c22cb871cb0542119eaa1f92dbead623
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

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